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Zwitterionic spirocycles based on dinitrobenzofurazan and tropolone heteroanalogs

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Abstract

Zwitterionic spirocyclic σ-complexes were synthesized by reaction of 7-chloro-4,6-dinitrobenzofurazan with 2-(benzylamino)cyclohepta-2,4,6-trien-1-one, 2-(benzylamino)cyclohepta-2,4,6-triene-1-thione, and N-benzyl-7-(benzylimino)cyclohepta-1,3,5-trien-1-amine. The structure, stereodynamics, and stability of the spirocycles were studied by NMR spectroscopy, X-ray analysis, and DFT quantum chemical calculations at the B3LYP/6-31G** level of theory. The contribution of heteroatoms to positive charge delocalization and the thermodynamic and kinetic stabilities of the spirocycles increase in the series aminotropone < aminothiotropone < aminotropone imine.

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Authors and Affiliations

  1. Southern Federal University, ul. Zorge 7, Rostov-on-Don, 344090, Russia

    A. V. Tkachuk, S. V. Kurbatov, O. N. Burov, M. E. Kletskii, Yu. P. Tavunova, P. G. Morozov, V. A. Voronina & V. I. Minkin

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  1. A. V. Tkachuk
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  2. S. V. Kurbatov
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  3. O. N. Burov
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  4. M. E. Kletskii
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  5. Yu. P. Tavunova
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  6. P. G. Morozov
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  7. V. A. Voronina
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  8. V. I. Minkin
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Correspondence to A. V. Tkachuk.

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Original Russian Text © A.V. Tkachuk, S.V. Kurbatov, O.N. Burov, M.E. Kletskii, Yu.P. Tavunova, P.G. Morozov, V.A. Voronina, V.I. Minkin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1388–1393.

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Tkachuk, A.V., Kurbatov, S.V., Burov, O.N. et al. Zwitterionic spirocycles based on dinitrobenzofurazan and tropolone heteroanalogs. Russ J Org Chem 49, 1373–1378 (2013). https://doi.org/10.1134/S1070428013090248

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  • DOI: https://doi.org/10.1134/S1070428013090248

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